Bittersweet Mistakes
by iloveshoes
Summary: What happens when a simple friendly gesture, turns you into the worst friend ever? It makes you surprisingly happy. Rory and Dave
1. The innocent beggining

**Disclaimer: I don't own anything!!!!! So don't sue!**

Rory sighed loudly, she couldn't help it, it had just been that sort of week. One of those weeks that seems to clutter your mind with silly things, things that shouldn't be there in the first place. Rory Gilmore was stuck pondering where she had gone wrong? Normally she was so predictable (though she would deny it); but she had to face it she wouldn't ever even dream of what she had done. Until well…when she did it. She couldn't even talk to her mother, who she always talked to. She most certainly couldn't talk to her best friend. Her boyfriend was a; heck no! No, she sat by the window staring out onto the snow covered lawn, thinking to herself.

She had done terrible thing, a back stabbing, no good, sluttish thing! In her defense she hadn't intended for it to happen…but that really made no difference. She had kissed her best friends boyfriend! How it came about…well you'd have to start at the beginning.

_Rory had yawned loudly, it was seven thirty in the morning on a Saturday. Yet she was awake reading, Romeo and Juliet to be exact. She hear__d movement from up above, ignoring__ it, she turned her page. She could never get enough of these stories, the__y__ enthralled her._

_ There was some__one__ clunking beside, but she remained unfazed in the old beaten up couch. _

_"Rory Gilmore why are you awake?" demanded a shrill voice from beside her._

_Rory tearing her eyes away from her book looked up at the figure that was her mother. "I'm meeting lane," she replied._

_"This early?"_

_"Around ten," she shrugged._

_"So why, my dear rooster, are you up three hours early, dressed and ready to go?" smirked Lorelei staring at her daughters appearances. _

_"I had to take a shower before you did, you always take all the hot water, and our pipes are old and tired and they wouldn't have reheated in time for my shower!"_

_"I KNEW," shouted the mother triumphantly._

_"Knew what?"_

_"That my shower was colder than usual."_

_"My shower wasn't that long," said Rory indignantly. _

_"No I meant your icy personality brings down the temperature where ever you go, our pipes aren't old; they're just can't get warm while you live here."_

_"Are you suggesting I move out?"_

_"I bet you and Jack Frost would make an adorable couple!" She then stormed off into the kitchen to get coffee. Rolling her eyes Rory went back to her book. __Hoping to not be disturbed again till at least the next chapter.__ She heard her mother shout, __"YOU DRANK AL__L THE COFFEE," she wasn't going to get to go back to her reading any time soon._

_Sti__ll extremely vexed at her mother__ for forcing her to get up from her cozy couch and make her a whole pot of coffee__ like some slave child. And then have the nerve to state that it was taking much t__o__o much time to perk and she needed to get to the__ inn. Rory found herself still in a__ fit when she arrived at Al's pancake world. _

_"Rory," squealed her overly excited best friend Lane Kim. _

_"Hey," smiled Rory walking over to where she was sitting. Then she looked around confused, "why aren't we sitting in our usual table?"_

_"Because it only has two chairs.__"_

_"So?"_

_"So__…__didn't I tell you?"_

_"Tell me what?"_

_"We__l__l__…__Dave sort of wanted to hang out with me today, but I told him that I was chilling with you. And he totally looked all disappointed; and you know I can't resist his adorable brown eyes. So…I sort of told him he co__u__ld come along, that we weren't planning on doing anything girly. Of course he didn't want to impose he's so sweet like that…you're not mad are you?"_

_It was a lot to process, this coming from a girl who read fluently in Shakespearian__! Y__et sometimes her friend__'s__ rushed high pitched sentences still confused her. _

_"Yeah, no, that's cool," she replied once she sorted out the basis of Lane's point_. Dave was coming, hope you don't mind._ Seating herself and picking up a menu Rory idle wondered about Dave and Lane, they had been a sort of couple for a while now. Lane was __currently dating __Hueng__ Cho __(A/N I have no Idea how to spell his name, but ya'll know who I'm talking about). Some random Korean that Lane's mother had picked out for her. Granted Lane had no attachments to Hueng Cho what so ever, Rory still wondered if it bothered Dave. It would bother her if Jess had to pretend to date some other girl for his mom. __Then she paused…would it really?__ Sure__ she thought it would, but now…she wond__ered if she would honestly care.__ Her and Jess weren't that tight anymore. Things had defiantly gone downhill once they started dating. It was like the mystery was gone. _

_Dave came in a second later and sat down in bet__ween Rory and Lane. "Hey Rory, L__ane!" he smiled picking up his own menu. _

_Rory smiled in return, and stared at his face for a second, "His eyes weren't that adorable," she thought bitterly. She was a tad upset about Lane invited Dave on their day together, gees what was the point of being girls if you don't ever have girl time. _

_"So Dave," she said deciding it wasn't his fault. _

_"Yeah,"__ he asked looking up from his laminated menu. _

_"What college are you thinking about?"_

_"Uh…well I'm hoping Brown," he answered._

_"What? But that's far away?" stated Lane dumbly. "How would __that __work.__"_

_"Maybe you Cho could give you a ride to visit me sometime," he responded slightly coldly. _

_Rory looked down at her at her lap, she had defiantly started something. She honestly didn't mean to, she wasn't that mad. More like slightly annoyed, but not annoyed enough to purposely get them fighting. _

_"Hey now, you know momma Kim is the one making us go out, and pretty soon he'll break my heart, and she'll have to let me go out with you!"_

_"Yes, yes I know, we've been through it," he looked exhausted, Rory couldn't help but notice that he rubbed his forehead somewhat. She knew it then she was right it bothered Dave, how could it not, some girl he's crazy about; willing to do all this insanity for her. And she's still seeing another guy. That had to hurt. _

_"So Dave," Rory piped in trying to change the subject. "What are you going to study at Brown?"_

_"If I get in, I'm hoping to major in Medicine, and Minor in Music," he was now focusing on Rory ignoring Lane. _

_"Oh wow, you want to be a doctor?"_

_"Yeah, I'd like it, but it helps that my parents are willing to pay for half my schooling if I major in either Medicine or Law. And law bores me."_

_Rory laughed. "What medicine field do you want to go __into.__"_

_"Pediatrician."_

_"Awe, kids!" she squealed._

_"Yeah," he smiled._

_"I have to pee!" __Announced Lane suddenly throwing Dave and Rory out of their conversation._

_"Okay…?"_

_"Rory didn't you say you had to pee too?" she asked pointedly. _

_"Um yes," she answered confused. She figured she better stand up and go with Lane, even though she hadn't had a beverage since her morning coffee three hours ago. Come to think of it she was quite thirsty if anything. _

_The girls went into the girl's room Lane glared at a five year old girl washing her hands. "Come on little girl, you wasting water, you going to put us in a drought!"_

_Poor thing began to cry as she ran out of the room, "LANE!" shouted Rory starting to go after the girl. _

_Lane grabbed her arm and kept her from going after the girl, "I'll apologies later, me and you need to talk! Sabotage is happing at Starshallow High School!"_

_"What are you talking about?" laughed Rory watching a Lane freaking out. _

_"All these girls at school are totally hitting on Dave; they all think I'm with __Hueng__ Cho so I can't tell them to back off."_

_"Sure you can."_

_"They'd tell my mom."_

_"Why would they do that?"_

_"Because they are female."_

_"I'm female."_

_"Yes, but you're you Rory, and you wouldn't dream of sabotaging me."_

_"Well we are best friends."_

_"Exactly!" grinned Lane, "You as my BEST friend, can help me out!"_

_"How?"_

_"You can become friends with Dave!"_

_"How would that work?"_

_"You'd keep his at__tention off those other girls."_

_"You mean keep him distracted?"_

_"Well…yeah."_

_"Lane that's crazy!"_

_"Just till __Hueng__ Cho finally breaks up with me!"_

_"You can't be serious," she shouted taken very__ taken__ aback._

_"Come on Rory, you're my best friend! You're the only one who can help me!" _

_"But…you want me to keep Dave attention away from other girls?" sighed Rory giving in._

_"Yes!"_

_"How?"_

_"Talk about me, tell him how awesome I am, and tell me when he starts to get upset about __Hueng__ Cho." Rory nodded only because she didn't want to tell Lane that he already was upset. _

_"I guess we can hang out tomorrow after school," shrugged Rory._

_"Thank you, Thank you, __thank__ you!" Lane squeezed her friend appreciatively befor__e bouncing back into the restaur__ant. Dave sat waiting patiently, staring idly around the diner. Rory sort of felt bad for him, he looked lonely._


	2. Comics and Coffee

_Her cheeks were pink, her lips were blue, her eyes were puffy, but her insides were warm. A large cup of coffee was the reason for the warmth, the fact that it was Connecticut in December was the reason for everything else. She was walking side by side__ with__ Dave__ she was drinking her preferred beverage (coffee)__, he__was __drink__ing his;__ Hot chocolate. They had fought for quite some time over coffee. He felt that it was destroying her health. She felt it was the only thing keeping her from strangling him, so she of course won. Boys were easy!_

_But now they were on their way to the local book store, Dave didn't really question why Rory wanted to hang out with him randomly. __Lane had probably told him some lie, __like Rory needed__ to approve__ of him__, or something__ stupid like that_

_"So why are we headed to the book store again?" he asked before sipping his drink._

_"Well book stores are happy places Dave, and I'm still upset over the coffee incident__," she replied teasingly. _

_"They have books," he announced._

_"Most bookstores door," she nodded._

_"Why don't we go some__where__ more fun, like __not a bookstore__?"_

_"We can go to __"__chucky cheese__"__ later Da__vey,__"__ she laughed as__t__hey had reached their location; she opened the door to the small shop and went in smirking. He clumped in after her. _

_The__ room smelt of mold__ and __cinnamon__-__the Christmas scent of the week. Kirk__ liked to__ keep things fresh. He had recently been employed at the local bookstore, Lorelei and Rory had a bet on how long it would be till he was employed at the Luke's. So far he had worked__ almost everywhere else in town;__ Lorelei thought Luke would eventually crack, Rory didn't agree. Luke was too tough and didn'__t have a __high __tolerance__ for people in the town__, plus he wasn't hiring. He had Jess_

_Speaking of, Rory felt a little odd not going to Luke's to get coffee this morning; she didn'__t feel like seeing Jess. He had__ acting moody__ lately (more than usual);__ probably had some spat with Luke. Rory didn't want to bring Dave into Jess' problems either. So she had suggested they go back to Al's to get something to drink. Though Al's coffee wasn't nearly as good as Luke's! Dave didn't really have an opinion __considering__ all he was getting was childish hot chocolate. _

_"Oh my gawd!__ I love this book," Rory squealed pulling out a large__ novel and showing it to hi__m. _

_"Put it on your Christmas list," he suggested._

_"__I already own it."_

_"Then why are you looking at hear,"_

_"Cause it's exciting, it's like finding my book's long lost twin!" she told him looking through to pages._

_"His twin__'s__ little on the heavy side, I hope they aren't identical."_

_"__Yes, they are Identical, and__ did you just call my book fat?" she demanded glaring at him._

_"No I called is twin fat," Dave answered taking the book from her, "I can barely lift this thing!"_

_"Don't blame the book for your girly muscles," she shot back snatching the book away from him and slipping it back into his hallow place on the shelf. _

_"__I don't have…hey they have comic books!" His eyes had fallen on the isle completely dedicated to comics. The Row was completely filled with superman, Spiderman, batman and basically any other "man" you could think of. _

_"Duh!"_

_"I don't shop here," he defended walking over to the section filled with little animated drawings. Slowly he pulled out a comic that read, "X-man" on the front. _

_"Who do you think would win in a fight, spider-man or batman?"_

_"Batman would win the first battle, but then spider-man would come back and kick his ass in rematch. But if we're talking reality; they'd be tag team partners." _

_Rory smiled slightly, it was fun to not be the dork for once. Whenever she was with her mother, she was the dork (smarts wise), Lane was a __rebelling __drummer__ so she wasn't a dork, __and Jess__ was too much of the brooding bad boy to be a dork. So it always fell on her, but now as Dave scanned through his little plastic book, she was the normal one. _

_(Five minutes later)_

_The two young souls were back in the cold making their way down the street. Dave had purchased a few comics and was trying to explain to Rory how Rouge's powers' worked. "If she touches you she sucks the life out of you," he repeated__ for the seventh time. _

_"I know I understand that__ I just don't understand how that gives her other people's powers, I mean sure she can take Bobbie'__s powers while they're kissing, but __once they stopped kissing wouldn't she not have his power."_

_"It has a bit of a delay to wear off."_

_"Your books are complicated," she told him laughing as she__ glanced both ways before crossing the street. _

_"At least they're light weight, and portable!"_

_"Are you going back to making cracks at my book?"_

_"All I'__m saying is that book was huge __and the print was tiny." _

_"All the more fun," she retorted pulling her coat on tighter._

_"I give up," he shrugged, "It's a losing battle!"_

_"Why do you even bother in the first place?"_

_"Purely for entertainment," Dave answered._

_She couldn't help but flash him large smile as they made their way to her __house. He had band practice the__r__e__ and she had homework. _

_"So this was fun," he told her as they walked down her drive way._

_"It was," she agreed, "Maybe next time I'll convince you to drink grown up drinks with me."_

_"Next time?"__ Dave repeated raising an eyebrow, a __small smile playing on his lips_

_"Yes, we should hang out again some time."_

_"__MmKay__,"__ he smiled looking at his feet as he walked. It was a sort of awkward moment, but it was also a comfortable awkward moment. It made no sense, but yet there it was hanging in the air, and Rory found __herself__ quite at ease. _


	3. Bored Games, Cary Grant and Kisses

**Disclaimer: I don't anything but a laptop and a toothbrush, so please don't sue!**

(authors note) I updated! Yay. I was bored and my school has been light this week so I thought I'd add as chapter. Tada!

_Rory chewed on her pencil. Dave was coming over and they were going to watch Cary Grant movies, starting with her favorite "bringing up baby." He had never seen a bunch of them, she felt it her duty as his friend to educated him. _

_The two of them had hung out several time lately. In fact, Lane had even mentioned to Rory that she spent more time with her boyfriend then his girlfriend did. Thus, Rory tried to spread out her and Dave's get togethers. However, she couldn't help but plan this when he mentioned the only Cary Grant movie he had ever seen was "Charade." This was horrible news. He had read so many comic books and never seen "North by North West." Her mother had agreed it was tragedy indeed. So she invited him over. She also was thoughtful enough to invite Lane. Of course Lane accepted and planned on telling her mom that Rory would be only one present that day. _

_The problem was, the reason Rory sat on the couch nibbling on a pencil, was that Lane had just called. Her mom hadn't given her permission to come. Apparently an aunt of Lane's was in town. Lane was supposed to spend the day at home. Lane had asked Rory to call Dave and cancel the movie day for her. Her mom would get suspicious if she called "Rory" twice in a row to cancel. _

_Calling Dave would be an easy thing. Just pick up the phone, punch in his numbers. Let it ring. Wait for his oddly unique voice to answer. Say, "Sorry Dave, Lane can't come today. We'll have to reschedule." Then he'd reply, "Oh that's too bad. Well, better luck next time." Not that her and Dave's conversations sounded like a poorly written play._

_Still, there was the option of not calling Dave. She let her eyes slide towards the clock on the VCR. Dave was supposed to arrive at her house in twenty minutes. Would it be so bad, if her Dave did the movie day without Lane? She hadn't seen in him in a while fearing Lane would get upset. It wasn't her fault that a good friend of hers was dating her best friend. She could always say, he didn't answer his phone, so he showed up. And since he was already there, they just went ahead and watched one movie. It really wouldn't hurt. So putting pencil down Rory ignored the phone sitting in it's cradle and put the disk into the DVD player. Putting in popcorn, I realized I was being selfish for the time in my life. What was one movie going to hurt? _

_Twenty minutes later Dave arrived. Rory of course then realized that she had to tell Dave that Lane wasn't coming. Would he leave? Well, if he did it was just as well. So she took in a deep breath as he entered the living room and plopped on the sofa. _

"_Um, Lane can't come," she blurted out. _

"_Oh." Was all he said. _

"_Her aunt is in town," she explained. _

"_Which side?" he asked. _

"_Mothers."_

"_How many sisters can that lady have?" He asked incredulously? _

"_I don't know. I'm an only child." Rory answered sitting next to him. _

"_I'm one of five, and three of us our boys," he noted, "So what are we watching first."_

_Rory was glad that he didn't care that Lane wasn't coming. He didn't ask if they should reschedule. He, just as she did, saw no reason why they shouldn't be allowed to watch a movie without Lane nuzzled between them. _

"_Bringing up Baby," smiled Rory grabbing the remote. _

"_Cary Grant knocks someone up?" he asked looking totally shocked._

"_Not exactly," she laughed turning the TV on and hitting play. _

_Three movies later they were both leaning against each other, watching yet another Cary Grant movie, "Philadelphia Story." An empty bowl of popcorn sat between them with a few soda cans laying all over the coffee table. "I love James Stewart," announced Rory grabbing the remote to turn the volume up. The heater had just kicked on and it was extremely noisy. _

"_I like Katherine Hepburn," was Dave's reply. _

"_You only say that, because if you say that you like James Stewart I'll make fun of you for being gay," Rory giggled. _

"_That plus, she is apparently a goddess. Who the hell doesn't love goddesses?" _

"_Their sisters?"_

"_How so?" _

"_Well, Jan Brady had enough trouble with being Marsha's sister. Imagine being the little sister of goddess?"_

"_True. It would be a lot to live up to," agreed Dave nodding his head. "Good thing you are an only child then," he teased._

"_Shut up, I am far from perfect, Mister."_

"_Oh I'm sorry, did you not make your bed today?" He chuckled removing the popcorn bowl from between them._

"_No! I did make my bed, but I have a library book sitting on my desk. It was due tuedays."_

"_Holy cow! You are in so much trouble! I am calling your mom. Ms. GILMORE!" He shouted. _

"_Be quiet you'll disturb the neighbors"_

"_LORELAI!" He continued. "RORY IS ON THE PATH OF DESTRUCTIVENESS."_

"_No, stop!" she whimpered sitting up to quiet him. "Seriously my neighbors are nosy!"_

"_Then let them come in here and give you a lift to the library. For there is a book in that room in need of saving. From you the EVIL QUEEN!" He shouted. "MS. GILMORE!"_

_That was it, Rory put her hand over his mouth. He looked at her with wide eyes, then he squinted at her. _

"_Will you be quiet?" she asked._

_He shook his head no. "Then I can't very let you go," she said repositioning herself to so that she was leaning forward over him. She glared at him and he glared back. Finally he nodded. "You won't yell?"_

_He nodded. _

_She removed her and he smiled up at her. "See now isn't this more fun."_

"_No," he said stubbornly. "You know what is more fun? Clue!"_

"_Clue?" she repeated. _

"_Yeah. My mom and me used to play it," he exclaimed._

"_Not starting off so well," she told him._

"_It is an amazing game. I always figuring out who did it," he bragged. _

"_There's something to put on your resume," she told him sarcastically. _

"_I hope it get's me into Harvard!"_

"_Why would you want to go Harvard?" She laughed he didn't seem like the type._

"_If you are going there, I don't see why I shouldn't get to go! It seems like a stand up school," he told her._

"_It's drama school isn't as good as Yale's, but is decently respectable," She agreed. _

"_Well, now how am I supposed to become a big famous movie star at Harvard then? I guess I'll have to go to Yale. Well then?"_

"_Well then, what?" She was confused._

"_You'll go to Yale if I go there right?"_

"_Why should I?"_

"_I was gong to go to Harvard for you, the least you can do is go to Yale for me!" he said offended._

"_I suppose, but you see I'm not so good at clue. Monopoly is more of my thing, do you think it'll get me in?" _

"_As long as you are a business major," he informed her _

"_Then it's settled." They both were silent for a minute just staring at each other. She hadn't realized how close they had been sitting. She could smell him and he smelled good. "Hi," he whispered after what seemed like forever._

"_Hi." she replied just as quietly. It wasn't something she could explain, one second they had been talking about fake college plan. The next second all she could think of was, how his eyes were especially blue in the shirt he was wearing. _

"_Hi." he repeated._

_She smiled, "You just said that."_

"_I wasn't sure if you heard me,"_

"_I did."_

"_Well I…"he leaned forward a little. Rory didn't lean in herself, but she didn't lean back. He leaned in more till he was an inch from her. She still didn't move, her eyes were glued on his. She let them drop down and look at his mouth then back up at his eyes. He pressed his lips on hers. They were soft and perfect. She pulled away a little at first, merely from shock. Then without really thinking about it she leaned in herself. She was kissing Dave and she liked it. His hand was suddenly warm on her cheek, stroking her skin with his thumb. She brought her own hand up to his the back of his head and played intertwined her fingers into his hair. This went on for several minutes till suddenly he wrenched himself away. _

"_I should go!" he announced. _

_Rory was starting to panic as well. "That's probably good."_

"_Yeah. Okay. Bye." He stood up and walked out of the room. Rory remained seated. She heard the front door open and close, but she didn't move. She had just kissed or well made out with her best friend's boyfriend. What was wrong with her? She was a horrible person. She deserved to be shot. Put in jail, at least fined for the book on her desk. But she knew that the librarian never fined her. She liked Rory too much. Rory was just about to go upstairs and kill herself when there was a knock at the door. She prayed it wasn't Lane. She stood slowly and went to front door. She opened it without looking to see who it was. _

_It was Dave he stood on her doorstep nervously. "I forgot my…um.. Jacket," he pointed to the couch. Where sure enough ir laid draped over the back. He made and awkward movement to get in the door way. He paused then without much hesitation he grabbed Rory by the waist and kissed her again. She had never been kissed like this. Dean's kisses were gentle and almost pouring. Jess's kisses were aggressive and demanding, but not in the fun way. More in the way that made you feel like you were being used. _

_Dave kisses weren't to angry and moody, but they weren't simple and dull. They were passionate and explosive. She didn't want them to ever stop. Instead of stopping the kiss and saying, "Dave we can't!" Rory was selfish for the second time that day. She put her arms around Dave's neck and kicked the door closed with her foot. _


End file.
